Department of Chemistry and Biochemistry, The University of Southern Mississippi, 118 College Drive No. 5043, Hattiesburg, Mississippi 39406, USA.
J Org Chem. 2012 Dec 7;77(23):10925-30. doi: 10.1021/jo3015903. Epub 2012 Nov 12.
A straightforward stereoselective and enantiodivergent cyclization strategy for the construction of γ-lactams is described. The cyclization strategy makes use of chiral malonic esters prepared from enantiomerically enriched monoesters of disubstituted malonic acid. The cyclization occurs with the selective displacement of a substituted benzyl alcohol as the leaving group. A Hammett study illustrates that the cyclization is under electronic control. The resulting γ-lactam can be readily converted into a novel proline analogue.
本文描述了一种构建γ-内酰胺的立体选择性和对映体发散的环化策略。该环化策略利用从取代的丙二酸单酯制备的手性丙二酸酯。环化反应选择性地取代取代的苄醇作为离去基团。哈米特研究表明，环化反应受电子控制。所得γ-内酰胺可以很容易地转化为新型脯氨酸类似物。
